2-Amino-4-methylpyridine → HCID 84292551, compound

HRID 1392120Notes

Reaction equation

HRID 1392120 reaction equation
[Li]CCCC.[NH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][N:8]=1.C([O:16][C:17]([C:19]1[N:23]2[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]2=[N:21][C:20]=1[CH3:29])=O)C.[Cl-].[NH4+]>O1CCCC1>[CH3:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:17]([C:19]2[N:23]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]3=[N:21][C:20]=2[CH3:29])=[O:16])[CH:12]=1

Participants

6

Reactant 4

HCID 15332-Amino-4-methylpyridineHCID 25517Ammonium ChlorideHCID 682232ethyl 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxylateHCID 178418339Butyllithium

Product 1

HCID 84292551HCID 84292551, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

37 ml n-BuLi (1.6 M in hexane) were added dropwise to a solution of 3.2 g 2-amino-4-methylpyridine in 57 ml tetrahydrofuran (THF) at 0° C., while stirring. After warming to room temperature, the mixture was stirred for one hour. The reaction solution was cooled to −78° C., 5.8 g 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester, dissolved in 10 ml THF, were slowly added dropwise, and the mixture was stirred for one hour. After addition of 60 ml ammonium chloride at room temperature, the mixture was extracted with methylene chloride, the organic phases were dried over sodium sulfate, and the solvent was removed. The product was purified by boiling and precipitation in hexane and was obtained with a yield of 68%.

Workup

  1. stirringthe mixture was stirred for one hour
  2. temperatureThe reaction solution was cooled to −78° C.
  3. additionwere slowly added dropwise
  4. stirringthe mixture was stirred for one hour
  5. extractionthe mixture was extracted with methylene chloride
  6. dry with materialthe organic phases were dried over sodium sulfate
  7. customthe solvent was removed
  8. customThe product was purified
  9. customprecipitation in hexane
  10. customwas obtained with a yield of 68%

Sources & evidence

ORD record
ord-75504b41ac9a49eea2ed5f5c56a7727a
Source dataset
uspto-grants-2008_03
Patent number
US07342025B2

Reaction notes

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